White Light/NIS‐Promoted Aminoselenylation of Alkenes by Using N‐Tosylhydrazones. Issue 16 (28th March 2023)

• Record Type: Journal Article
• Authors: Chen, Xianlie; Zhao, Ping; Zeng, Qingle
• Is Part Of: European journal of organic chemistry. Volume 26:Issue 16(2023)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2023-03-28
• Subjects: aminoselenylation -- iodosuccinimide -- photochemical reaction -- three component reaction -- tosylhydrazones; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202300043
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A white light/iodosuccinimide (NIS)‐promoted three component reaction of alkenes, N ‐sulfonylhydrazones, and diorganyl diselenides for synthesis of organylselenylethyl sulfonylhydrazones under air is disclosed. This intermolecular aminoselenylation of alkenes using N ‐tosylhydrazones as nitrogen source was performed under mild conditions and well tolerated for common groups. In addition, heteroaryl and aliphatic diselenides also gave the target compounds. Gram‐scale reaction also carried out smoothly. This protocol has a wide range of substrates and affords moderate to high yields and excellent regioselectivities. The photoactive intermediates from the interaction between NIS and diphenyl diselenide was detected by UV‐visible absorption spectra, which matches the wavelength of the applied white LED. A reasonable mechanism was proposed based on UV‐visible light experiments and control experiments. Abstract : A three component reaction of alkenes, N‐ tosylhydrazones, and diorganyl diselenides for the synthesis of organylselenylethyl sulfonylhydrazones is disclosed, in which 42 products were synthesised in moderate to excellent yields (51 %–85 %). In addition, the reaction proceeded well at room temperature in air, without any metal, using ethyl acetate as an environmentally benign solvent.